“Do You Know Who You Look Like?”

It’s a peculiar sociological fact: whenever two people walk around town together, one will inevitably say the name of some establishment they’re passing, for absolutely no reason. This name won’t be a New York Post-ian pun, and it won’t inspire a cute story about the place’s wares. Instead, someone will just sort of belch the name out (“Beacon’s Closet!”), thereby acknowledging its fleeting purchase on his or her attention. (“This exists, I guess!”) Such utterances are not without siblings; plenty of equally fruitless observations arrive with the flimsiest bit of prompting and even less regard for how they’ll be received. Perhaps the least useful of such outbursts, however, is the celebrity doppelgänger notification.

In the same way that there’s no real reason to simply say what you see when looking at signage, seldom does it prove worthwhile to say who you see when gazing into the genetic cauldron of someone’s face. Still, people tell friends and also total strangers which famous people they look like all the time — as though gifting them with an Inception-style totem so as not to forget some deeper truth. It’s a conversational gambit whose best-case scenario is “mild enthusiasm,” and it has to stop.

That person you think looks like Lizzie Caplan — hopefully a lady — she may be a huge Party Down fan, but even then there’s little payoff to pointing out the resemblance. Nobody has ever been so bowled over by a bit of fawning analysis as to install its messenger as chief consigliore, a font of advice and trusted confidante. Telling someone the person whose stunt double they could pass for is merely an exercise in hopeful flattery that will never go over better than the actual underlying sentiment — something along the lines of “You are attractive in a familiar way.”

Flattery is often the culprit for comparison, either in a misguided effort to lift spirits or to spit some seriously tired game. It’s not the only reason, though. For some of us, nearly every passing thought now begs to be unshackled from brain-prison and set upon the townspeople like RT-able Stay Puft marshmallow men. It’s hard to ignore that thunderclap eureka-moment when you think you’ve got something good, or just keep it to yourself. Also, it’s fun to puzzle out which famous people might have jointly entered Jeff Goldblum’s teleportation machine from The Fly to create a separate third entity. (My high school principal looked exactly like Tommy Lee Jones blended with Tweety Bird.) However, actually telling someone who it is that they look like can backfire in any number of exciting ways.

It’s impossible to bring up this next point and not have it come across like the 9/11 of humblebrags, but here goes: people sometimes tell me I look like famous people. The appraisals are uniformly flattering, too — most often it’s Tom Cruise or, like, the idea of Superman — but it’s still an awkward thing to hear. Because how to respond? “Yes, I do look like Tom Cruise, and my thetan levels are commensurate. Furthermore, nanu nanu.” It’s a bad look, owning the comparison, because then you might as well have made it yourself, like some kind of monster. But dismissing it outright isn’t much better; doing that suggests you think about such things way too much and probably have some unresolved self-esteem stuff, too. So, obviously, it’s become old hat for me to assure men and women I do not think I resemble the Man of Steel in any way. Getting told such things doesn’t really bother me, though. The real bother is often reserved, it seems, across gender lines in the other direction.

I learned long ago never to tell a lady what celebrity she looks like. Not unless she asks outright, and maybe even then don’t do it. It’s not that men aren’t vain, touchy creatures — we very much are — it’s just an issue we tend to make less hay about. Anyway, like many social rules of thumb, I learned this one via irreversible error, during the great Kelly Osbourne calamity of 2002. The less said about that fateful night, the better. But in the intervening years, I’ve learned that it’s not only what are perceived as unflattering comparisons that can leave women as cold as the eyes of Kelly Osbourne; rather, there are many similar ways to go about doing that.

Let’s say, for instance, that a lady actually does favor Lindsay Lohan. There’s a better chance of the troubled actress retiring because she hates people paying attention to her, than of someone who legit looks like Lindsay Lohan not being constantly told about the similarity. There’s no breaking new ground here. In fact, telling a dead ringer about her Mean Girl-match means taking a handful of much trod-upon old ground and flinging it at her feet. It’s as rote and perfunctory as asking somebody named Vicki Lohan or whatever if there’s any relation. The only natural response is a polite smile and quiet contempt, the kind that both of you remember for the next several stilted interactions.

Something else to consider is that you could be just plain old wrong. You never actually tell a person who they look like; you only tell them who you think they look like — and perhaps reality disagrees. Or maybe you’re not wrong, but the person has no idea who you’re talking about. Nothing kills an idea’s momentum quite like when two people aren’t on the same page. If you tell your friend that she looks like Rebecca Hall, and then you have to explain who that is while Google Image-ing, it won’t even matter how spot-on you are — because to your friend, Rebecca Hall could be anybody. The only way your attempt at a compliment could go worse is if it has racial undertones, like telling your Indian friend she looks like Padma Lakshmi, which more or less counts as a third-degree hate crime.

Against my better judgment, I recently told somebody who she looked like, for the first time in 11 years. In doing so, I discovered a new way for it to backfire horribly. One of my colleagues is an attractive, happily married woman with almost violently red hair built out of sunsets. It’s important to note also that I had just consumed five seasons of dearly departed heartland drama Friday Night Lights, co-starring flawless queen Connie Britton — she of the similarly scorching ginger tresses. It wasn’t just the hair, though; there is a certain rough-edged kindness in the eyes of both that radiates compassion and competence in equal measure. If ever there was a slam-dunk, I thought, this was it. I was wrong.

I informed my co-worker about who she had clearly been separated at birth from, and received a chilly glare. A fourth-quarter buzzer went off in my head. Inexplicably, it was Code: Osbourne all over again. “Isn’t Connie Britton like 45?” she asked, seizing on the one thing I hadn’t taken into account when racing through a very rudimentary decision-tree mere moments before. “I’m 10 years younger than her,” my colleague continued. She wasn’t upset, but I definitely hadn’t made her day — I’d merely made it more awkward. Coach Taylor was going to have my ass for this. Although my co-worker later conceded that, yes, Connie Britton is an objectively attractive person, age be damned, the distance between intent and reaction was staggering.

Telling someone which celebrity she looks like is less a compliment than a compliment-flavored observation, with a cringe-y aftertaste. Except if the intention is, in fact, to be complimentary, and not to deliver breaking mind-news, this vessel is somewhat limiting. It assigns the recipient physical beauty only by proxy. It tells her that her attractiveness ends where Anne Hathaway’s begins. It’s kind of patronizing. Of course, none of that really matters on a day when you’re happy to receive whatever compliment you can get. But that’s the final problem with telling people who’s DNA they seem to share — if we tell them often enough, they’ll freak the fuck out when we eventually stop.